A new stereoselective synthesis of (Z)-9-tricosene, the sex attractant of the common housefly

Muscalure (9/tricosene) was prepd. very readily by an instant-ylid reaction of nonanal with Ph3P:CH(CH2)12Me or of (Z)-Me(CH2)7CH:CHCH2OAc with BrMg(CH2)11Me. (Z)-9-Tricosene was formed in a highly selective manner (.apprx.97.5) although it was difficult to assess the Z/E-ratio with accuracy. [on SciFinder (R)]